197508-95-5

Upstream product

• 447-61-0 2-Trifluoromethylbenzaldehyde 
• 2386-64-3 ethylmagnesium chloride 
• 557-20-0 diethylzinc 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 104384-69-2 2-bromo-1-[2-(trifluoromethyl)phenyl]propan-1-one 
• 16185-96-9 1-(2-(trifluoromethyl)phenyl)propan-1-one 

Relevant academic research and scientific papers

2,2′-Bipyridine-α,α′-trifluoromethyl-diol ligand: Synthesis and application in the asymmetric Et2Zn alkylation of aldehydes

A chiral 2,2′-bipyridine ligand (1) bearing α,α′-trifluoromethyl-alcohols at 6,6′-positions was designed in five steps affording either the R,R or S,S enantiomer with excellent stereoselectivities, i.e. 97% de, >99% ee and >99.5% de, >99.5% ee, respectively. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alcohol using (S)-ibuprofen as the resolving agent. An initial application for the 2,2′-bipyridine-α,α′-CF3-diol ligand was highlighted in the ZnII-catalyzed asymmetric ethylation reaction of aromatic, heteroaromatic, and aliphatic aldehydes. Synergistic electron deficiency and steric hindrance properties of the newly developed ligand afforded the corresponding alcohols in good to excellent yields (up to 99%) and enantioselectivities (up to 95% ee). As observed from single crystal diffraction analysis, the complexation of the 2,2′-bipyridine-α,α′-CF3-diol ligand generates an unusual hexacoordinated ZnII.

Diminished reactivity of ortho-substituted phenacyl bromides toward nucleophilic displacement

A systematic increase of substitution rates by tert-butylamine on α-bromopropiophenones is observed with meta or para substituents with increasing electron-withdrawing ability (k x 103 L M-1 min-1 = 12.7 (p-CH3), 15.7 (o-F), 20.5 (H), 20.0 (p-Cl), 23.6 (m-Cl), 27.3 (p-CF3)). Within an ortho-substituted series, the reactivities decrease (k x 103 L M-1 min-1 = 7.64 (o-OCH3), 5.31 (o-CH3), 2.85 (o-Cl), 2.40 (o-CF3)). Ortho-substitution results occur from rotational barrier effects and an Aδσ + Bδσ + repulsion. The major bonding contribution between reaction and α-substituent centers (A-B) is only the σ bond. When π bonding is allowed between A and B (meta/para-substitution), delocalization and stabilization of the reacting center occurs.

Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants

Some novel 2-methyl-3-aminopropiophenones were synthesized and their centrally acting muscle relaxant activities were,evaluated for an inhibitory effect on the flexor reflex in rats. The structure-activity relationships are discussed. In this series 2-methyl-3-pyrrolidino-1-(4-trifluoromethylphenyl)-propan-1-one (28) showed significant centrally acting muscle relaxant activity. In addition, the activities of each enantiomer (28-(S) and (R)) were studied along with their acute toxicities. Compound 28-(R) was found to exhibit more potent activity and weaker acute toxicity than 28-(S). Accordingly, compound 28-(R) (NK433) is under development as a novel centrally acting muscle relaxant.